Best Stops on a Florida Keys Road Trip Itinerary

I can’t believe we’ve never written about our Florida Keys road trips. But we haven’t! Dave and I have driven to Key West from Miami three times (plus once to Key Largo) and we’ve shared some fun things to do in Key West but we’ve never really shared what it is like to drive along this 100 mile long stretch of highway over the sea. So we thought that it was about time to share some of our favorite stops on a road trip from Key Largo to Key West. So, shall we take a drive to the southernmost point of the United States?

Florida Keys Road Trip

The Florida Keys Overseas Highway is 113 miles long through the Florida Keys from the United States mainland to Key West. This chain of islands off the southern coast of Florida divide the Atlantic Ocean from the Gulf of Mexico. As you head south, you are surrounded by water. The drive from Miami to Key West, truly is one of the great road trips in the world.

The drive from Miami to Key West can be done in 3 1/2 hours but to really appreciate it, you should take your time and spend the night on a couple of Keys before reaching your final destination. Once you get to the south of the mainland, the road trip begins just past Florida City crossing over Jewfish Creek. I’m not going to lie, crossing that first bridge is thrilling. It feels like we’re heading to the Caribbean but instead of a five hour flight, we’re driving to the tropics!

Driving to the Florida Keys – Plan Your Trip

We highly recommend renting a car in Miami for your Florida Keys Road Trip. We have also driven to Key West from Fort Lauderdale Airport. Check Rental Car Comparisons at CarRentals.com

Get your Key West Overseas Highway Self Driving Tour that highlights the top attractions from Miami to Key West including Hollywood landmark the African Queen riverboat as you follow the route of the historic Overseas Railway to Plantation Key, the smuggler’s haven. It gives tips to check out Big Betsy, the giant lobster, and Theatre of the Sea. The trip then takes you through Islamorada and on to Anne’s Beach, Long Key, and Marathon until you reach Key West.

Tolls: Florida has a lot of toll roads and we suggest getting a SunPass. All tolls in Florida are collected electronically if you don’t have a Sun Pass, you will be billed utilizing the TOLL-BY-PLATE system where you will be charged a $25 fee on top of the toll. Check the Florida Turnpike website for details.

About the Overseas Highway

There are 42 bridges connecting 34 Florida Keys with the most famous being the Seven Mile Bridge at Marathon. We had always wanted to drive this southernmost stretch of US Highway 1 since watching True Lies in 1994 and when we finally did, it lived up to the hype. We had to get on that highway that goes to the sea. It is truly the coolest thing to drive over these bridges located in the middle of the sea.

Built in the 1930s the Overseas Highway followed the East Coast Railroad line which was damaged by a hurricane. Thanks to that feat of engineering, 3 million visitors make their way to the Florida Keys each year, and Dave and I were part of those millions.

It’s easy to find attractions and things to do on the Overseas Highway by following the mile markers. The road is well marked with Mile Marker zero located in Key West. When driving south from Key Largo, you’ll be counting down from mile marker 106 letting you know how far you have to go to Key West. Nice!

Now that you have a bit of background on the highway, let’s see what there is to do on a Florida Keys Road Trip.

Where to Stay in the Florida Keys

There are many places to stay in the Florida Keys from Key Largo to Key West. But in high season it can be nearly impossible to book a room without reservations. We suggest choosing a place to stay and making it your home base to explore the Keys.

Once you are in the Florida Keys, it’s easy to explore. With Key Largo being the northernmost island, you may want to move on to Islamorada or Marathon. They are a little more central and you can drive from key to key. We have suggested hotels on each island that that we highlight.

• You can skip directly to where to stay in the Florida Keys at each section:

Top Things to See on a Key West Road Trip

One of the best tips we can give for taking a Florida Keys Road Trip is to avoid high season and long weekends when driving. If you do need to drive during this time, go late at night or before sunrise to beat the traffic. Our first time driving to Key West from Miami, we never made it past Key Largo. Traffic was at a halt and we decided to stay put.

But luckily, there are plenty of things to do in Key Largo, so our first introduction to the Florida Keys was a lot of fun.

Key Largo

Key Largo is pretty awesome. We literally sat in traffic for hours before giving up. Movies and songs have been written about Key Largo and you can stop at the Caribbean Club is a fun stop that is the oldest bar in the upper keys. Dating back to 1938, The Caribbean Club has seen a lot of action most notably hosting Humphrey Bogart and Lauren Bacall in the film Key Largo. It’s still a family run business and a great place to stop for some Key Lime Pie, a Bloody Mary or to listen to some live music.

John Pennekamp Coral Reef State Park

If you are looking to have an adventure, John Pennekamp Coral Reef State Park is one of the top things to do in Key Largo. It is home to the only living coral reef in the United States and if you want to explore underwater, this is the place to go. What makes snorkelling or scuba diving different in Key Largo is that you can dive to see “Christ of the Abyss” a nine-foot-tall underwater statue of Christ located in just 25 feet of water off the coast of Key Largo.

Book this snorkeling tour from Key Largo – this half day tour takes you to the most beautiful locations in the Florida Keys National Marine Sanctuary and Pennekamp State Park. Explore the coral reefs of Molasses, Elbow, French Reef and the famous Christ of the Abyss on Dry Rocks. When we’ve been snorkeling in the keys we saw, sea turtles, eagle rays, moray eels and there is a good chance you will see them as well.

Florida Keys State Parks

There are 11 State Parks in the Florida Keys and a unique way to explore them is to ride the Florida Keys Overseas Heritage Trail. This trail follows the historic Henry Flagler railway bridges connecting the Keys. There are campgrounds on some of the State Parks making a Florida Keys Road trip much more affordable if you can camp as you make your way down.

• Some notable ones to visit besides John Pennekamp Coral Reef State Park (above) are:
  • Windley Key Fossil Reef Geological State Park – Islamorada
  • Long Key State Park – This park was highly affected by Hurricane Irma but there are still a few campsites
  • Bahia Honda State Park – Some great campsites, kayaking and beaches
  • Fort Zachary Taylor State Park – this state park has the best beach in Key West and it is a historic fort with Civil War artifacts on hand.

The Fish House

A great stop for lunch is the Fish House to grab a staple Florida Keys dish of Conch Fritters, fish tacos and Florida lobster and stone crab. It’s a great atmosphere and has been a Key Largo staple since 1982. We enjoyed a starter of coconut shrimp followed by a delicious portion of Mahi Mahi.

Alabama Jack’s

Another quirky place that can only be found en route to the Florida Keys is Alabama Jacks. Popular with motorcyclists Alabama Jack’s is located under Card Sound Bridge which is the old toll road on an alternate route from Florida City. Instead of taking Highway 1, take 905A card sound road. But be warned, you need to have cash to cross the toll bridge. Alabama Jack’s renowned for its conch fritters and has a great atmosphere sitting on two barges among the mangroves. It’s always a happening place. Located at 58000 Card Sound Road.

Mrs. Mac’s Kitchen

For a unique and delicious slice of Key Lime Pie head to Mrs. Mac’s Kitchen that was so good its become famous in the upper keys. You can order a whole key lime pie to go!

Where to Stay in Key Largo

• Luxury – Playa Largo Resort – The Playa Largo Resort and Spa has luxury rooms, bungalows and a beach house. You can book many Key West water sports at the hotel.
• Mid Range – Key Largo Marriott Beach Resort – You can never go wrong with a Marriott. It’s our favourite mid to upper range hotel chain. It has an onsite marina and dive shop offering plenty of water sports to book at the hotel.
• Budget – Dove Creek Resort and Marina –

Moving on from Key Largo – Luckily we had the chance try our Florida Keys Road Trip two more times and I am happy to say that we made it to Key West each time. With each trip, we saw more and our latest trip was just a few months before COVID-19 hit. We look forward to going back to do more.

Islamorada Key

The next island on your Florida Keys Road Trip will surprise you. I loved Islamorada Key so much, we wrote an entire article about all the things to do. But just in case you don’t want to click off of our drive, let’s go through all the top things you cannot miss on Islamorada.

Robbies Marina is the place to be on Islamorada with watersports, restaurants, bars and attractions, it is a place you can spend the entire day.

Feed the Tarpon

A unique thing to do on Islamorada is to feed the tarpon at Robbies. After nursing an injured Tarpon way back in 1976, the friendly Tarpon named Scarface came back again and again for some food and to say hello. He eventually brought his friends and the tarpon have been coming to the docks ever since to leap out of the water for a tasty treat.

Parasailing

Parasailing in the Florida Keys is an amazing way to see the bridges and keys from above. It’s a gorgeous view to see the bridges spanning over blue waters with islands dotting the landscape. You can make out the coral reefs and it truly is a blast. If you’ve never gone parasailing before, this is the place to do it. Parasailing with Sundance Watersports. 

Robbies Marina

Enjoy the day hanging out at Robbies Marina. There’s a great restaurant, outdoor shops and plenty of water sports leave from here. We had breakfast at Robbies, and even though it was early in the day, we had a slice of Key Lime Pie. You can never get enough Key Lime pie in the Florida Keys.

Other things to do on Islamorada

If you want to do some shopping, head into Rain Barrel Sculpture Gallery at Rain Barrel Village, it top Florida Keys destination for more than 40 years. You can’t miss it, just look for the giant rock lobster out front. If you are staying over or have a designated driver, don’t miss hitting the beer garden of the Florida Keys Brewing Company. We loved sampling their microbrews.

Where to Stay in Islamorada

Islamorada is a great place to make a base before heading farther south. From here you can explore Duck Key, Lower Matecumbe Key to the South and Plantation Key to the North.

Postcard Inn at Holiday Isle – This is the most popular place to stay on Islamorada offering cottages and rooms with Marina and Atlantic Ocean views. There are water sports on site and you can book scuba diving, glass bottom boat tours, and snorkeling trips. It also has the popular Tiki Bar on the beach so even if you aren’t staying there, make sure to have a cocktail or slice of Key Lime Pie at this world famous location.

Hadley House Resort – We stayed at Holiday House Resort a boutique resort with cottages. I would recommend staying at the building overlooking the water. Cottages are set back from the sea and the hotel building seemed much better. Your $25 resort fee covers use of Stand up paddleboards and kayaks. There’s parking and a pool.

Marathon

Marathon is a city that spreads across several Florida Keys. Starting just past Duck Key it spans across seven keys: Knight’s Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key islands.

We haven’t spent a lot of time on Marathon but it is a popular place to visit in the keys. From the Dolphin Research Center to Aquarium Encounters it has all the makings for a good family vacation. Marathon is also the gateway to Seven Mile Bridge and Pigeon Key Island. There are some nice beaches on Marathon Key as well, Sombrero Beach and Coco Plum Beach are good places to hang out. And there is a dog park which is a good stop if you are traveling with pets.

Turtle Hospital

What we recommend visiting is the Turtle Hospital. The Turtle Hospital is one of the most popular stops on a Florida Keys Road Trip to see the work that goes into rehabilitation injured sea turtles. We love supporting projects like this and proceeds for your guided tour and entrance go to help saving the turtles.

Keys Fisheries

Make sure to stop at Keys Fisheries for lunch. We enjoyed chillaxing on the outdoor patio. It’s a fast food joint where you order from a window and then find a picnic table in the packed restaurant. Get the grilled Mahi Mahi, Conch Chowder or its signature dish, the Lobster Reuben.

Seven Mile Bridge

Leaving Marathon Key, Seven Mile Bridge is largest segmental bridge in the world! This long bridge connects the upper Keys to the Lower Keys. Make sure to take the ferry across to Pigeon Key that was a former work camp of the Florida East Coast Railway. You can catch the ferry over from Pigeon Key Gift Shop at mile marker 48.

Where to Stay on Marathon Key

Marathon has a lot of options for accommodation and is more affordable than Key West. You can find hotels ranging from luxury to budget. A lot of people take day trips to Key West from Marathon.

Bahia Honda Key and Big Pine Key

You have now entered the Lower Keys. You’ve made it farther than most, so keep going! Coming across 7 Mile Bridge, most people b-line it to Key West as it’s most likely been a long drive, but this is a great place to stop for at least a few hours.

At least stop at Big Pine Key to view the unique wildlife. Did you know that there is wild deer in the Florida Keys? Big Pine Key houses the endangered Key deer, and are protected by National Key Deer Refuge Nature Center. These small deer actually swim between islands!

If you like beaches, you are going to love Bahia Honda Key. Bahia Honda State Park has camping but note: As of now, the Sandspur Beach remains closed for day use and camping during construction to repair damage from Hurricane Irma.

No Name Pub

While on Big Pine Key, stop for lunch at No Name Pub. This stop is worth it just to see the dollar bills hanging from its ceiling. No Name Pub dates back to 1931 when it was a fishing store. In 1936 they a restaurant was added and the No Name Pub was born. They have certainly taken the tradition of displaying your first dollar earned on the wall, it seems that anyone who has visited the pub has left dollar bills on the ceiling. There’s even some euro and CAD dollars too.

Key West

Congratulations! You’ve made it to your final destination on your Florida Keys Road Trip. Key West is a great place to spend a few days taking in the Caribbean atmosphere. Key West no longer feels like the United States, it feels like a little slice of the tropics.

Southernmost Point

The first thing most visitors do in Key West is head to the Southernmost Point marker. This is the southernmost point on mainland USA and everyone that makes it to Key West stops here for their required photo op.

Watch Sunset at Mallory Square

Mallory Square is one of the most happening places in Key West and it is an excellent spot to watch sunset over the Gulf of Mexico. There are plenty of things to do in Mallory Square as well, so be sure to head over there during the day. If you are looking for a fun adventure, book a sunset tour on Aqua bikes to enjoy views of Sunset Key and Key West from the water. You can even bring two drinks along with you.

• The Maritime Museum – The Mel Fisher Heritage Maritime Museum displays many artifacts from the 17th-century ships.
• The Waterfront Playhouse – The longest-running theatre in Florida has nightly rotating shows all year long.
• Key West Shipwreck and Treasure Museum – There’s a 65-foot lookout tower, shipwreck artifacts and actors recreating the 17th century feel dressed in period clothing. Book your ticket in advance 
• The memorial sculpture garden is located directly in front paying tribute to famous patrons of the theatre and residents. Take a stroll through the lines of sculptures of famous residents including busts of Ernest Hemingway, Harry S Truman, Tennessee Williams, and many other important people.

Duval Street

It’s no secret that people come to Key West for partying, and Duval Street is the place to do it. You can go bar hopping all night long on Duval Street. Some of our favorites are Jimmy Buffet’s Margaritaville, (no trip to Key West would be complete without visiting Jimmy Buffet’s) and the Hard Rock Cafe, Lucy’s Retired Surf Bar, Sloppy Joes, Virgillios, Rick’s Café, and our personal favorite The Wine O Bar and Lounge.

If you want to join a tour of Duval Street to see the top bars and restaurants while making new friends, check out this fantastic pub crawl tour that stops at five top rated pubs with a cocktail at each stop.

Get on the Water

Adventure lovers will enjoy Key West and if you don’t get on the water, you’ll be missing out. An excellent tour is to book an eco-tour to explore Key West Wildlife Refuge. Go kayaking through the mangroves, enjoy snorkeling at John Pennekamp Coral Reef State Park and enjoy a sail on an eco-friendly catamaran with Honest Eco Tours. 

• Book this top-rated Sunset Tour tour here free from worries as tours can be canceled up to 24 hours in advance with a full refund.
• Look for more water and sunset tours here with Get Your Guide to find your choice of floating bars, schooners, and catamarans that will take you out to watch the stunning sunsets. They offer last-minute bookings and full refunds on cancellations within 24 hours of the tour.

One of our favourite things to do in Key West was to visit the Located (113km) 70 miles from Key West, the Dry Tortugas is one of the most remote national parks in the United States. Read all about it at Our Key West Vacation with IHG Rewards Club Points

Dolphin Watching

200 bottlenose dolphins live in the warm waters off the Florida Keys and you can take a dolphin watching tour or we had it as part of our Honest Eco Tour. When booking a dolphin or wildlife tour be sure to use a sustainable recognized tour operator like Honest Eco Tours based out of Key West or You Can book this Dolphin Watch and Snorkeling Tour in Advance.

Mile Marker 0

Well you made it! All the way to Mile Marker 0, the bottom of the United States. It is customary to grab a selfie at this sign located on Whitehead Street just south of Duval Street. You’ve earned it. This is the end of the line and a popular place to make note that you have completed your Florida Keys Road trip from Key Largo to Key West. Wasn’t it amazing?

Where to Stay in Key West

La Concha Crown Plaza is the perfect place to stay in the heart of the action, is located directly on Duval Street. The lobby is walking distance from all the top key west attractions. There’s a pool for guests only. There is a luxurious rooftop spa and gorgeous sunset views. Check for Reviews and pricing on TripAdvisor / Booking.com

Perry Hotel Key West is a quiet retreat on the marina of Stock Island. Stock Island is an extension of Key West that feels worlds away. This boutique hotel has elegant rooms overlooking the waterfront. What we loved about it was the local vibe. Check it out on TripAdvisor / Booking.com

When to do a Florida Keys Road Trip

We have taken a road trip to Key West in October, November and December. December is way too busy and you are going to have the highest prices.

November is a quieter time and the weather is great. You can also find more affordable accommodation and tours aren’t booked up.

December to February is high season and you’ll have higher prices and a lot of crowds. But you are pretty much guaranteed good weather.

Late February to April is another good time to visit for lower rates.

June to November is hurricane season and it is important to plan accordingly. Hurricane Irma did extensive damage to the Florida Keys in 2017 but it has recovered nicely. That said, we’ve been to the Keys in October and had amazing weather. he summer months are hot and wet.

We were also in Key West for Fantasy Fest in October. This is a busy time, but it is a unique time to visit to see the crazy characters that walk the streets.

And these are our top stops on a Florida Keys road trip from Miami to Key West. The Florida keys are so abundant, it will take several trips to really see them all. Let us know what we missed and we’ll be sure to add it on during our next rip.